Citation: Xu Ci, Xu Jianchao, Liu Han, Li Xuechen. Development of aspartic acid ligation for peptide cyclization derived from serine/threonine ligation[J]. Chinese Chemical Letters, ;2018, 29(7): 1119-1122. doi: 10.1016/j.cclet.2018.03.012 shu

Development of aspartic acid ligation for peptide cyclization derived from serine/threonine ligation

Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Hong Kong, China

Corresponding author: Li Xuechen, xuechenl@hku.hk

Received Date: 13 February 2018
Revised Date: 24 February 2018
Accepted Date: 8 March 2018
Available Online: 9 July 2018

Figures(5)

Based on a mechanism analogous to the serine/threonine ligation, the aspartic acid ligation, which is facilitated by the γ-amino alcohol based ligation and oxidation, is developed and applied to the synthesis of cyclic peptides. The γ-hydroxyl group triggers the ring-chain tautomerization via a 6-endo-trig process, while the δ-hydroxyl group facilitates the oxidative cleavage of the vicinal diol to give carboxylic acid.
- Aspartic acid ligation,
- Peptide cyclization,
- Serine/threonine ligation,
- Ring-chain tautomerization,
- Acyl transfer,
- Selective oxidation
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